Colorant compounds

ABSTRACT

A compound of the formula 
     
       
         
         
             
             
         
       
     
     wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R, Y, CA, A − , m and n each, independently of the others are as defined herein.

Cross-reference is made to the following co-pending applications:

Co-pending application U.S. Serial No. (not yet assigned; AttorneyDocket No. 20060161Q-US-NP), filed concurrently herewith, entitled“Phase Change Inks Containing Colorant Compounds,” with the namedinventor Jeffery H. Banning, the disclosure of which is totallyincorporated herein by reference, discloses a phase change inkcomposition comprising a phase change ink carrier and a colorantcompound of the formula

Co-pending application U.S. Serial No. (not yet assigned; AttorneyDocket No. 20060167-US-NP, filed concurrently herewith, entitled“Colorant Compounds,” with the named inventor Jeffery H. Banning, thedisclosure of which is totally incorporated herein by reference, andCo-pending application U.S. Serial No. (not yet assigned; AttorneyDocket No. 20060167Q-US-NP), filed concurrently herewith, entitled“Phase Change Inks Containing Colorant Compounds,” with the namedinventor Jeffery H. Banning, the disclosure of which is totallyincorporated herein by reference, discloses a phase change inkcomposition comprising a phase change ink carrier and a colorantcompound of the formula

BACKGROUND

The present disclosure is generally related to colorant compounds. Morespecifically, the present disclosure is directed to colorant compoundsparticularly suitable for use in hot melt or phase change inks. Oneembodiment of the present disclosure is directed to a compound of theformula

wherein R₁, R₂, R₃, and R₄ each, independently of the others, is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group, wherein R₁ and R₂ can bejoined together to form a ring, wherein R₃ and R₄ can be joined togetherto form a ring, and wherein R₁, R₂, R₃, and R₄ can each be joined to aphenyl ring in the central structure; wherein a and b each,independently of the others, is an integer which is 0, 1, 2, or 3,wherein each R₅, and R₆ independently of the other, is (i) an alkylgroup, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylarylgroup, (v) a halogen atom, (vi) an ester group, (vii) an amide group,(viii) a sulfone group, (ix) an amine group or ammonium group, (x) anitrile group, (xi) a nitro group, (xii) a hydroxy group, (xiii) a cyanogroup, (xiv) a pyridine or pyridinium group, (xv) an ether group, (xvi)an aldehyde group, (xvii) a ketone group, (xviii) a carbonyl group,(xix) a thiocarbonyl group, (xx) a sulfate group, (xxi) a sulfide group,(xxii) a sulfoxide group, (xxiii) a phosphine or phosphonium group,(xxiv) a phosphate group, (xxv) a mercapto group, (xxvi) a nitrosogroup, (xxvii) an acyl group, (xxviii) an acid anhydride group, (xxix)an azide group, (xxx) an azo group, (xxxi) a cyanato group, (xxxii) anisocyanato group, (xxxiii) a thiocyanato group, (xxxiv) anisothiocyanato group, (xxxv) a urethane group, (xxxvi) a urea group, or(xxxvii) hydrogen, wherein R₅ and R₆ can each be joined to a phenyl ringin the central structure,

wherein R₈, R₉, and R₁₀ each, independently of the other, is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group;

wherein R is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkylgroup, or (iv) an alkylaryl group, wherein R if an alkyl group has fromabout 1 to about 100 carbon atoms, or about 18 to about 33 carbon atoms,or about 30 carbon atoms, or about 50 carbon atoms, wherein R if an arylgroup has from about 5 to about 20 carbon atoms, or about 6 carbon atomsor about 10 carbon atoms, wherein R if an alkylaryl group has from about7 carbon atoms, or about 30 carbon atoms, or about 50 carbon atoms orabout 100 carbon atoms, wherein R if an arylalkyl group has from about 7carbon atoms, or about 30 carbon atoms, or about 50 carbon atoms, orabout 100 carbon atoms, wherein in embodiments, R is a waxy chain, waxyas used herein meaning containing at least about 10 carbon atoms, or atleast about 18 carbon atoms, or from about 18 to about 100 carbon atoms,or from about 18 to about 33 carbon atoms, wherein in embodiments R isC₆H₅ (phenyl), wherein in embodiments R is CH₂CH₂ (ethylene), wherein inembodiments R is OH, wherein in embodiments R is O—R (alkoxy), forexample, in embodiments, R is O—CH₃ (methoxy), wherein in embodiments Ris OAc, wherein OAc refers to any acetate moiety, and wherein inembodiments R is a co-polymer of maleic anhydride;

wherein n is an integer which is about 1 to about 1000, or about 1 toabout 20 or at least about 4, or at least about 12, or at least 50, andwhere m is an integer which is about 1 to about 1000, or about 1 toabout 20, or at least about 4, or at least about 12, or at least about50.

In general, phase change inks (sometimes referred to as “hot melt inks”)are in the solid phase at ambient temperature, but exist in the liquidphase at the elevated operating temperature of an ink jet printingdevice. At the jet operating temperature, droplets of liquid ink areejected from the printing device and, when the ink droplets contact thesurface of the recording substrate, either directly or via anintermediate heated transfer belt or drum, they quickly solidify to forma predetermined pattern of solidified ink drops. Phase change inks havealso been used in other printing technologies, such as gravure printing,as disclosed in, for example, U.S. Pat. No. 5,496,879 and German PatentPublications DE 4205636AL and DE 4205713AL, the disclosures of each ofwhich are totally incorporated herein by reference.

Phase change inks for color printing typically comprise a phase changeink carrier composition which is combined with a phase change inkcompatible colorant. In a specific embodiment, a series of colored phasechange inks can be formed by combining ink carrier compositions withcompatible subtractive primary colorants. The subtractive primarycolored phase change inks can comprise four component dyes, namely,cyan, magenta, yellow and black, although the inks are not limited tothese four colors. These subtractive primary colored inks can be formedby using a single dye or a mixture of dyes. For example, magenta can beobtained by using a mixture of Solvent Red Dyes or a composite black canbe obtained by mixing several dyes. U.S. Pat. No. 4,889,560, U.S. Pat.No. 4,889,761, and U.S. Pat. No. 5,372,852, the disclosures of each ofwhich are totally incorporated herein by reference, teach that thesubtractive primary colorants employed can comprise dyes from theclasses of Color Index (C.I.) Solvent Dyes, Disperse Dyes, modified Acidand Direct Dyes, and Basic Dyes. The colorants can also includepigments, as disclosed in, for example, U.S. Pat. No. 5,221,335, thedisclosure of which is totally incorporated herein by reference. U.S.Pat. No. 5,621,022, the disclosure of which is totally incorporatedherein by reference, discloses the use of a specific class of polymericdyes in phase change ink compositions.

Phase change inks have also been used for applications such as postalmarking, industrial marking, and labeling.

Phase change inks are desirable for ink jet printers because they remainin a solid phase at room temperature during shipping, long term storage,and the like. In addition, the problems associated with nozzle cloggingas a result of ink evaporation with liquid ink jet inks are largelyeliminated, thereby improving the reliability of the ink jet printing.Further, in phase change ink jet printers wherein the ink droplets areapplied directly onto the final recording substrate (for example, paper,transparency material, and the like), the droplets solidify immediatelyupon contact with the substrate, so that migration of ink along theprinting medium is prevented and dot quality is improved.

Compositions suitable for use as phase change ink carrier compositionsare known. Some representative examples of references disclosing suchmaterials include U.S. Pat. No. 3,653,932, U.S. Pat. No. 4,390,369, U.S.Pat. No. 4,484,948, U.S. Pat. No. 4,684,956, U.S. Pat. No. 4,851,045,U.S. Pat. No. 4,889,560, U.S. Pat. No. 5,006,170, U.S. Pat. No.5,151,120, U.S. Pat. No. 5,372,852, U.S. Pat. No. 5,496,879, EuropeanPatent Publication 0187352, European Patent Publication 0206286, GermanPatent Publication DE 4205636AL, German Patent Publication DE 4205713AL,and PCT Patent Application WO 94/04619, the disclosures of each of whichare totally incorporated herein by reference. Suitable carrier materialscan include paraffins, microcrystalline waxes, polyethylene waxes, esterwaxes, fatty acids and other waxy materials, fatty amide containingmaterials, sulfonamide materials, resinous materials made from differentnatural sources (tall oil rosins and rosin esters, for example), andmany synthetic resins, oligomers, polymers, and copolymers.

British Patent Publication GB 2 311 075 (Gregory et al.), the disclosureof which is totally incorporated herein by reference, discloses acompound of the formula

wherein X1 is an ester group or an amide group (such as of a carboxylicor sulfonic acid) or a fatty amine salt of a sulfonic acid, each X2independently is a substituent, m has a value of from 0 to 2, Y1 and Y2are each independently H, alkyl, or halo, each Z independently is anester or amide group, and A- is an anion. The compound is useful as acolorant for toners, D2T2 printing, plastics, polyesters, nylons, andinks, especially ink jet or hot melt inks.

U.S. Pat. No. 1,991,482 (Allemann), the disclosure of which is totallyincorporated herein by reference, discloses a process of producingrhodamine dyes which comprises condensing a halogenated primary amine ofthe benzene series with fluorescein dichloride and sulfonating thecondensed product.

U.S. Pat. No. 5,013,857 (Bemeth et al.), the disclosure of which istotally incorporated herein by reference, discloses a process for thepreparation of sulpho-free triphenyl-methane dyestuffs.

U.S. Pat. No. 5,847,162 (Lee et al.), the disclosure of which is totallyincorporated herein by reference, discloses a class of4,7-dichlororhodamine compounds useful as fluorescent dyes having thestructure

wherein R₁-R₆ are hydrogen, fluorine, chlorine, lower alkyl loweralkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, loweralkoxy, lining group, or combinations thereof or, when taken together,R₁ and R₆ is benzo, or, when taken together, R₄ and R₅ is benzo; Y₁-Y₄are hydrogen or lower alkyl or, when taken together, Y. and R₂ ispropano and Y₂ and R₁ is propano, or, when taken together, Y₃ and R₃ ispropano and Y₄ and R₃ is propano; and X₁-X₃ taken separately areselected from the group consisting of hydrogen, chlorine, fluorine,lower alkyl carboxylate, sulfonic acid, —CH₂OH, and linking group. Inanother aspect, the disclosure includes reagents labeled with the4,7-dichlororhodamine dye compounds, including deoxynucleotides,dideoxynucleotides, and polynucleotides. In an additional aspect, thedisclosure includes methods utilizing such dye compounds and reagentsincluding dideoxy polynucleotide sequencing and fragment analysismethods.

U.S. Pat. No. 4,935,059 (Mayer et al.), the disclosure of which istotally incorporated herein by reference, discloses basic rhodamine dyessuitable for use in recording fluids for the ink jet process and forcoloring paper stock having the formula

where L is C₂-C₁₀-alkylene, R₁, R₂, and R₃ are each independently of theothers hydrogen, substituted or unsubstituted C₁-C₁₀-alkyl orC₁-C₇-cycloalkyl or R₁ and R₂ together with the nitrogen atom linkingthem together are a hetero cyclic radical, An- is one equivalent of ananion and m and n are each independently of the other 0 or 1.

U.S. Pat. No. 4,647,675 (Mayer et al.), the disclosure of which istotally incorporated herein by reference, discloses compounds of thegeneral formula

where A- is an anion, R is hydrogen or unsubstituted or substitutedalkyl or cycloalkyl, R₁ and R₂ independently of one another are eachhydrogen or unsubstituted or substituted alkyl or cycloalkyl, or one ofthe radicals may furthermore be aryl, or R₁ and R₂, together with thenitrogen atom, form a saturated heterocyclic structure, the radicals R₃independently of one another are each hydrogen or C₁-C₄-alkyl, R₄ and R₅independently of one another are each unsubstituted or substituted alkylor cycloalkyl, or one of the radicals may furthermore be hydrogen, arylor hetaryl, R₄ and R₅, together with the nitrogen atom, form a saturatedheterocyclic structure, n is 1, 2 or 3, X is hydrogen, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy or nitro and Y is hydrogen orchlorine, are particularly useful for dyeing paper stocks.

U.S. Pat. No. 1,981,515 (Kyrides), the disclosure of which is totallyincorporated herein by reference, discloses intermediates for rhodaminedyestuffs.

U.S. Pat. No. 1,981,516 (Kyrides), the disclosure of which is totallyincorporated herein by reference, discloses intermediates for secondaryalkylated rhodamine dyes.

British Patent Publication GB 421 737, the disclosure of which istotally incorporated herein by reference, discloses dyes of therhodamine series which are prepared by condensingnaphthalene-2:3-dicarboxylic acid with a m-aminophenol in which thenitrogen group is substituted by one or two alkyl groups, the products,if desired, being sulphonated. The unsulphonated products may be used aslake colouring matters whilst the sulphonated dyes are acid wool dyes.In examples, (1) naphthalene-2:3-dicarboxylic acid is condensed withdiethyl-m-aminophenol in the presence of zinc chloride giving a productwhich dyes tannin-mordanted cotton in the same shade as Rhodamine B anda sulphonated product which dyes wool bluish-red shades; (2)monoethyl-m-aminophenol is used instead of the diethyl-m-aminophenol inexample (1), yielding a dye, which when sulphonated dyes wool red-orangeshades; (3) 2-ethylamino-p-cresol replaces the diethyl-m-aminophenol inexample (1), yielding a dye dyeing and printing tannin-mordanted cottonin shades similar to Rhodamine 69BS and when sulphonated dyeing woolred.

Japanese Patent Publication JP 61221265, the disclosure of which istotally incorporated herein by reference, discloses rhodamine compoundsof formula I

wherein R₁, R₃ are each lower alkyl; R₂ is lower alkyl, 10 C or higherlong-chain alkyl; R₄ is 10 C or higher long-chain alkyl; X— is an anion,or squarylium compounds of formula II

wherein R₂ is 10 C or higher long-chain alkyl. Example:3,6-(N,N′-diethyl-N,N′-dioctadecyl)diamino-9-(2-carboxyphenyl)xanthiliumperchlorate. Use: materials for molecular electronics, which aresuitable for use as materials for photoelectric converter, opticalmemory, etc. Preparation:2-(4-N,N′-diethylamino-2-hydroxybenzoyl)-benzoic acid, which is acondensate between N-ethyl-N-octadecyl-m-hydroxyaniline and phthalicanhydride, is reacted with N-ethyl-N-octadecyl-m-hydroxyaniline toobtain the compound of formula I. 3-HOC₆H₄N(Et)(CH₂)₁₇Me and phthalicanhydride were heated at 150° for 4 hours, treated with aqueous NH3, andthe amorphous intermediate mixed with aqueous HClO₄ forming a compoundof formula I (R=R₂=Et; R₁=R₃=C₁₈H₃₇; X=ClO₄), having λmax (MeOH) 550 nm.

U.S. Pat. No. 5,084,099 (Jaeger et al.), the disclosure of which istotally incorporated herein by reference, discloses modified phasechange ink compatible colorants which comprise a phase change inksoluble complex of (a) a tertiary alkyl primary amine and (b) dyechromophores, i.e., materials that absorb light in the visiblewavelength region to produce color having at least one pendant acidfunctional group in the free acid form (not the salt of that acid).These modified colorants are extremely useful in producing phase changeinks when combined with a phase change ink carrier, even though theunmodified dye chromophores have limited solubility in the phase changeink carrier. Thin films of uniform thickness of the subject phase changeink compositions which employ the modified phase change ink colorantsexhibit a high degree of lightness and chroma. The primary amine-dyechromophore complexes are soluble in the phase change ink carrier andexhibit excellent thermal stability.

U.S. Pat. No. 5,507,864 (Jaeger et al.), the disclosure of which istotally incorporated herein by reference, discloses a phase change inkcomposition that includes a combination of different dye types such asan anthraquinone dye and a xanthene dye, which is most preferably arhodamine dye. While each dye type is insufficiently soluble withrespect to favored carrier compositions to preserve color saturation inreduced ink quantity prints, the dye type combination permits increaseddye loading and maintains print quality. In a preferred embodiment ofthe disclosure, a favored carrier composition is adjusted to promote thecolored form of a preferred rhodamine dye (C.I. Solvent Red 49) andmixed with a preferred anthraquinone dye (C.I. Solvent Red 172) whoseconcentration is kept below a critical level to prevent post printedblooming. The resulting preferred phase change ink compositions providea magenta phase change ink with enhanced light fastness and colorsaturation, as well as good compatibility with preferred existingsubtractive primary color phase change inks.

U.S. Pat. No. 5,621,022 (Jaeger et al.), the disclosure of which istotally incorporated herein by reference, discloses a phase change inkcomposition wherein the ink composition utilizes polymeric dyes incombination with a selected phase change ink carrier composition.

U.S. Pat. No. 5,747,554 (Sacripante et al.), the disclosure of which istotally incorporated herein by reference, discloses an ink compositioncomprising a polyesterified-dye (I) or polyurethane-dye (II) with aviscosity of from about 3 centipoise to about 20 centipoise at atemperature of from about 125° C. to about 165° C. and represented bythe formulas

wherein A is an organic chromophore, Y is an oxyalkylene orpoly(oxyalkylene), R is an arylene or alkylene, n represents the numberof repeating segments, and is an integer of from about 2 to about 50,and p represents the number of chains per chromophore and is an integerof from about 1 to about 6.

U.S. Pat. No. 5,902,841 (Jaeger et al.), the disclosure of which istotally incorporated herein by reference, discloses a phase change inkcomposition wherein the ink composition utilizes colorant in combinationwith a selected phase change ink carrier composition containing at leastone hydroxy-functional fatty amide compound.

U.S. patent application Ser. No. 10/607,382, filed Jun. 26, 2003,published Jan. 20, 2005, of Jeffrey H. Banning et al., and U.S. Pat. No.6,860,931 of Jeffrey H. Banning et al., the disclosures of each of whichare totally incorporated by reference herein, disclose in embodimentscompounds of the formulae

wherein R1, R2, R3, and R4 each, independently of the others, is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group, wherein R1 and R2 can bejoined together to form a ring, wherein R3 and R4 can be joined togetherto form a ring, and wherein R1, R2, R3, and R4 can each be joined to aphenyl ring in the central structure, a and b each, independently of theothers, is an integer which is 0, 1, 2, or 3, c is an integer which is0, 1, 2, 3, or 4, each R5, R6, and R7, independently of the others, is(i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv)an alkylaryl group, (v) a halogen atom, (vi) an ester group, (vii) anamide group, (viii) a sulfone group, (ix) an amine group or ammoniumgroup, (x) a nitrile group, (xi) a nitro group, (xii) a hydroxy group,(xiii) a cyano group, (xiv) a pyridine or pyridinium group, (xv) anether group, (xvi) an aldehyde group, (xvii) a ketone group, (xviii) acarbonyl group, (xix) a thiocarbonyl group, (xx) a sulfate group, (xxi)a sulfide group, (xxii) a sulfoxide group, (xxiii) a phosphine orphosphonium group, (xxiv) a phosphate group, (xxv) a mercapto group,(xxvi) a nitroso group, (xxvii) an acyl group, (xxviii) an acidanhydride group, (xxix) an azide group, (xxx) an azo group, (xxxi) acyanato group, (xxxii) an isocyanato group, (xxxiii) a thiocyanatogroup, (xxxiv) an isothiocyanato group, (xxxv) a urethane group, or(xxxvi) a urea group, wherein R5, R6, and R7 can each be joined to aphenyl ring in the central structure,

R8, R9, and R10 each, independently of the others, is (i) a hydrogenatom, (ii) an alkyl group, (iii) an aryl group, (iv) an arylalkyl group,or (v) an alkylaryl group, provided that the number of carbon atoms inR1+R2+R3+R4+R5+R6+R7+R8+R9+R10 is at least about 16, each Q,independently of the others, is a COOH group or a SO3H group, each Q-,independently of the others, is a COO— group or a SO3- group, d is aninteger which is 1, 2, 3, 4, or 5, A is an anion, and CA is either ahydrogen atom or a cation associated with all but one of the Q- groups,provided that when

at least one of the following of (a), (b), and (c) is true: (a) thenumber of carbon atoms in R1+R2+R3+R4 is at least about 42, (b) at leastone of R1,R2, R3, and R4 is a group of the formula

wherein R41 and R42 each, independently of the other, is an alkyl group,an aryl group, an arylalkyl group, or an alkylaryl group, or (c) atleast one of R1, R2, R3, and R4 is a branched alkyl group having atleast about 19 carbon atoms.

While known compositions and processes are suitable for their intendedpurposes, a need remains for new magenta colorant compositions. Inaddition, a need remains for magenta colorant compositions particularlysuitable for use in phase change inks. Further, a need remains formagenta colorants with desirable thermal stability. Additionally, a needremains for magenta colorants that exhibit minimal undesirablediscoloration when exposed to elevated temperatures. There is also aneed for magenta colorants that exhibit a desirable brilliance. Inaddition, there is a need for magenta colorants that exhibit a desirablehue. Further, there is a need for magenta colorants that are ofdesirable chroma. Additionally, there is a need for magenta colorantsthat have desirably high lightfastness characteristics. A need alsoremains for magenta colorants that have a desirably pleasing color. Inaddition, a need remains for magenta colorants that exhibit desirablesolubility characteristics in phase change ink carrier compositions.Further, a need remains for magenta colorants that enable phase changeinks to be jetted at temperatures of over 135° C. while maintainingthermal stability. Further, a need remains for magenta colorants for usein solid ink printers that operate with lower print head temperaturesmuch lower than 135° C. as well as in ultraviolet radiation curablesystems. Additionally, a need remains for magenta colorants that enablephase change inks that generate images with low pile height. There isalso a need for magenta colorants that enable phase change inks thatgenerate images that approach lithographic thin image quality. Inaddition, there is a need for magenta colorants that exhibit oxidativestability. Further, there is a need for magenta colorants that do notprecipitate from phase change ink carriers. Additionally, there is aneed for magenta colorants that do not, when included in phase changeinks, diffuse into adjacently printed inks of different colors. A needalso remains for magenta colorants that do not leach from media such asphase change ink carriers into tape adhesives, paper, or the like. Inaddition, a need remains for magenta colorants that, when incorporatedinto phase change inks, do not lead to clogging of a phase change inkjet printhead. Further, there is a need for magenta colorants thatenable phase change inks that generate images with sharp edges thatremain sharp over time. Additionally, there is a need for magentacolorants that enable phase change inks that generate images whichretain their high image quality in warm climates. Further, there is aneed for magenta colorants that enable phase change inks that generateimages of desirably high optical density. Additionally, there is a needfor magenta colorants that, because of their good solubility in phasechange ink carriers, enable the generation of images of low pile heightwithout the loss of desirably high optical density. A need also remainsfor magenta colorants that enable cost-effective inks.

The appropriate components and process aspects of the each of theforegoing may be selected for the present disclosure in embodimentsthereof.

SUMMARY

The present disclosure is directed to a compound of the formula

wherein R₁, R₂, R₃, and R₄ each, independently of the others, is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group, wherein R₁ and R₂ can bejoined together to form a ring, wherein R₃ and R₄ can be joined togetherto form a ring, and wherein R₁, R₂, R₃, and R₄ can each be joined to aphenyl ring in the central structure;

wherein a and b each, independently of the others, is an integer whichis 0, 1, 2, or 3,

wherein each R₅, and R₆ independently of the other, is (i) an alkylgroup, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylarylgroup, (v) a halogen atom, (vi) an ester group, (vii) an amide group,(viii) a sulfone group, (ix) an amine group or ammonium group, (x) anitrile group, (xi) a nitro group, (xii) a hydroxy group, (xiii) a cyanogroup, (xiv) a pyridine or pyridinium group, (xv) an ether group, (xvi)an aldehyde group, (xvii) a ketone group, (xviii) a carbonyl group,(xix) a thiocarbonyl group, (xx) a sulfate group, (xxi) a sulfide group,(xxii) a sulfoxide group, (xxiii) a phosphine or phosphonium group,(xxiv) a phosphate group, (xxv) a mercapto group, (xxvi) a nitrosogroup, (xxvii) an acyl group, (xxviii) an acid anhydride group, (xxix)an azide group, (xxx) an azo group, (xxxi) a cyanato group, (xxxii) anisocyanato group, (xxxiii) a thiocyanato group, (xxxiv) anisothiocyanato group, (xxxv) a urethane group, (xxxvi) a urea group, or(xxxvii) hydrogen, wherein R₅ and R₆ can each be joined to a phenyl ringin the central structure,

wherein R₈, R₉, and R₁₀ each, independently of the other, is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group;

wherein R is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkylgroup, or (iv) an alkylaryl group, (v) an alkoxy group, (vi) an acetategroup, or (vii) a co-polymer of maleic anhydride;

wherein n is an integer which is about 1 to about 1000, and where m isan integer which is about 1 to about 1000;

wherein A is an anion; and

wherein CA is either a hydrogen atom or a cation.

In embodiments, R if an alkyl group has from about 1 to about 100 carbonatoms, or about 18 to about 33 carbon atoms, or about 30 carbon atoms,or about 50 carbon atoms, wherein R if an aryl group has from about 5 toabout 20 carbon atoms, or about 6 carbon atoms or about 10 carbon atoms,wherein R if an alkylaryl group has from about 7 carbon atoms, or about30 carbon atoms, or about 50 carbon atoms, or about 100 carbon atoms,wherein R if an arylalkyl group has from about 7 carbon atoms, or about30 carbon atoms, or about 50 carbon atoms, or about 100 carbon atoms,wherein in embodiments, R is a waxy chain, waxy as used herein meaningcontaining at least about 10 carbon atoms, or at least about 18 carbonatoms, or from about 18 to about 100 carbon atoms, or from about 18 toabout 33 carbon atoms, wherein in embodiments R is C₆H₅ (phenyl),wherein in embodiments R is CH₂CH₂ (ethylene), wherein in embodiments Ris OH, wherein in embodiments R is O—R (alkoxy), for example, inembodiments, R is O—CH₃ (methoxy), wherein in embodiments R is OAc,wherein OAc refers to any acetate moiety, and wherein in embodiments Ris a co-polymer of maleic anhydride.

DETAILED DESCRIPTION

The present disclosure is directed to compounds of the formulae

wherein R₁, R₂, R₃, and R₄ each, independently of the others, is (i) ahydrogen atom, (ii) an alkyl group (including linear, branched,saturated, unsaturated, cyclic, substituted, and unsubstituted alkylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, boron, phosphorus, and the like either may or may not bepresent in the alkyl group), in one embodiment with at least 1 carbonatom, in another embodiment with at least about 2 carbon atoms, in yetanother embodiment with at least about 6 carbon atoms, in anotherembodiment with at least about 8 carbon atoms, and in yet anotherembodiment with at least about 18 carbon atoms, and in one embodimentwith no more than about 55 carbon atoms, in another embodiment with nomore than about 30 carbon atoms, and in yet another embodiment with nomore than about 20 carbon atoms, although the number of carbon atoms canbe outside of these ranges, (iii) an aryl group (including unsubstitutedand substituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about6 carbon atoms, in another embodiment with at least about 10 carbonatoms, and in yet another embodiment with at least about 14 carbonatoms, and in one embodiment with no more than about 26 carbon atoms, inanother embodiment with no more than about 22 carbon atoms, and in yetanother embodiment with no more than about 18 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iv) an arylalkylgroup (including unsubstituted and substituted arylalkyl groups, whereinthe alkyl portion of the arylalkyl group can be linear, branched,saturated, unsaturated, and/or cyclic, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the alkyl portion and thearyl portion of the arylalkyl group), in one embodiment with at leastabout 7 carbon atoms, in another embodiment with at least about 12carbon atoms, and in yet another embodiment with at least about 18carbon atoms, and in one embodiment with no more than about 55 carbonatoms, in another embodiment with no more than about 30 carbon atoms,and in yet another embodiment with no more than about 20 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas benzyl or the like, or (v) an alkylaryl group (includingunsubstituted and substituted alkylaryl groups, wherein the alkylportion of the alkylaryl group can be linear, branched, saturated,unsaturated, and/or cyclic, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in either or both of the alkyl portion and the arylportion of the alkylaryl group), in one embodiment with at least about 7carbon atoms, in another embodiment with at least about 12 carbon atoms,and in yet another embodiment with at least about 18 carbon atoms, andin one embodiment with no more than about 55 carbon atoms, in anotherembodiment with no more than about 30 carbon atoms, and in yet anotherembodiment with no more than about 20 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as tolyl or thelike, wherein R₁ and R₂ can be joined together to form a ring, whereinR₃ and R can be joined together to form a ring, and wherein R₁, R₂, R₃,and R₄ can each be joined to a phenyl ring in the central structure,wherein in embodiments, at least one of R₁, R₂, R₃ and R₄ is an alkylgroup, wherein in embodiments, at least one of R₁, R₂, R₃ and R₄ is anaryl group;

a and b each, independently of the others, is an integer which is 0, 1,2, or 3, in embodiments, wherein a and b are each zero;

each R₅ and R₆, independently of the other, is (i) an alkyl group(including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkyl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the alkyl group), in one embodimentwith at least 1 carbon atom, and in one embodiment with no more thanabout 50 carbon atoms, in another embodiment with no more than about 30carbon atoms, and in yet another embodiment with no more than about 18carbon atoms, although the number of carbon atoms can be outside ofthese ranges, (ii) an aryl group (including unsubstituted andsubstituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about6 carbon atoms, and in one embodiment with no more than about 55 carbonatoms, in another embodiment with no more than about 30 carbon atoms,and in yet another embodiment with no more than about 18 carbon atoms,although the number of carbon atoms can be outside of these ranges,(iii) an arylalkyl group (including unsubstituted and substitutedarylalkyl groups, wherein the alkyl portion of the arylalkyl group canbe linear, branched, saturated, unsaturated, and/or cyclic, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either or both of the alkylportion and the aryl portion of the arylalkyl group), in one embodimentwith at least about 7 carbon atoms, and in one embodiment with no morethan about 55 carbon atoms, in another embodiment with no more thanabout 30 carbon atoms, and in yet another embodiment with no more thanabout 18 carbon atoms, although the number of carbon atoms can beoutside of these ranges, such as benzyl or the like, (iv) an alkylarylgroup (including unsubstituted and substituted alkylaryl groups, whereinthe alkyl portion of the alkylaryl group can be linear, branched,saturated, unsaturated, and/or cyclic, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the alkyl portion and thearyl portion of the alkylaryl group), in one embodiment with at leastabout 7 carbon atoms, and in one embodiment with no more than about 55carbon atoms, in another embodiment with no more than about 30 carbonatoms, and in yet another embodiment with no more than about 18 carbonatoms, although the number of carbon atoms can be outside of theseranges, such as tolyl or the like, (v) a halogen atom, such as fluorine,chlorine, bromine, iodine, or the like, (vi) an ester group, (vii) anamide group, (viii) a sulfone group, (ix) an amine group or ammoniumgroup, (x) a nitrile group, (xi) a nitro group, (xii) a hydroxy group,(xiii) a cyano group, (xiv) a pyridine or pyridinium group, (xv) anether group, (xvi) an aldehyde group, (xvii) a ketone group, (xviii) acarbonyl group, (xix) a thiocarbonyl group, (xx) a sulfate group, (xxi)a sulfide group, (xxii) a sulfoxide group, (xxiii) a phosphine orphosphonium group, (xxiv) a phosphate group, (xxv) a mercapto group,(xxvi) a nitroso group, (xxvii) an acyl group, (xxviii) an acidanhydride group, (xxix) an azide group, (xxx) an azo group, (xxxi) acyanato group, (xxxii) an isocyanato group, (xxxiii) a thiocyanatogroup, (xxxiv) an isothiocyanato group, (xxxv) a urethane group, (xxxvi)a urea group, or (xxxvii) hydrogen, wherein R₅ and R₆ can each be joinedto a phenyl ring in the central structure,

R₈, R₉, and R₁₀ each, independently of the others, is (i) a hydrogenatom, (ii) an alkyl group (including linear, branched, saturated,unsaturated, cyclic, substituted, and unsubstituted alkyl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in the alkylgroup), in one embodiment with at least 1 carbon atom, in anotherembodiment with at least about 2 carbon atoms, in yet another embodimentwith at least about 6 carbon atoms, in another embodiment with at leastabout 8 carbon atoms, and in yet another embodiment with at least about18 carbon atoms, and in one embodiment with no more than about 55 carbonatoms, in another embodiment with no more than about 30 carbon atoms,and in yet another embodiment with no more than about 20 carbon atoms,although the number of carbon atoms can be outside of these ranges,(iii) an aryl group (including unsubstituted and substituted arylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe aryl group), in one embodiment with at least about 6 carbon atoms,in another embodiment with at least about 10 carbon atoms, and in yetanother embodiment with at least about 14 carbon atoms, and in oneembodiment with no more than about 26 carbon atoms, in anotherembodiment with no more than about 22 carbon atoms, and in yet anotherembodiment with no more than about 18 carbon atoms, although the numberof carbon atoms can be outside of these ranges, (iv) an arylalkyl group(including unsubstituted and substituted arylalkyl groups, wherein thealkyl portion of the arylalkyl group can be linear, branched, saturated,unsaturated, and/or cyclic, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in either or both of the alkyl portion and the arylportion of the arylalkyl group), in one embodiment with at least about 7carbon atoms, in another embodiment with at least about 12 carbon atoms,and in yet another embodiment with at least about 18 carbon atoms, andin one embodiment with no more than about 55 carbon atoms, in anotherembodiment with no more than about 30 carbon atoms, and in yet anotherembodiment with no more than about 20 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as benzyl or thelike, or (v) an alkylaryl group (including unsubstituted and substitutedalkylaryl groups, wherein the alkyl portion of the alkylaryl group canbe linear, branched, saturated, unsaturated, and/or cyclic, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either or both of the alkylportion and the aryl portion of the alkylaryl group), in one embodimentwith at least about 7 carbon atoms, in another embodiment with at leastabout 12 carbon atoms, and in yet another embodiment with at least about18 carbon atoms, and in one embodiment with no more than about 55 carbonatoms, in another embodiment with no more than about 30 carbon atoms,and in yet another embodiment with no more than about 20 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas tolyl or the like, wherein in embodiments, the number of carbon atomsin R₁+R₂+R₃+R₄+R₅+R₆+R₈+R₉+R₁₀ is in one embodiment at least about 4, inanother embodiment at least about 16, in another embodiment at leastabout 18, in yet another embodiment at least about 20, in still anotherembodiment at least about 22, in another embodiment at least about 24,in yet another embodiment at least about 26, in still another embodimentat least about 28, in another embodiment at least about 30, in yetanother embodiment at least about 32, in still another embodiment atleast about 34, in another embodiment at least about 36, in yet anotherembodiment at least about 38, in still another embodiment at least about40, in another embodiment at least about 42, in yet another embodimentat least about 44, in still another embodiment at least about 46, inanother embodiment at least about 48, in yet another embodiment at leastabout 50, in still another embodiment at least about 52, in anotherembodiment at least about 54, in yet another embodiment at least about56, in still another embodiment at least about 58, in another embodimentat least about 60, in yet another embodiment at least about 62, in stillanother embodiment at least about 64, in another embodiment at leastabout 66, in yet another embodiment at least about 68, in still anotherembodiment at least about 70, and in another embodiment at least about72,

wherein R is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkylgroup, or (iv) an alkylaryl group, wherein R if an alkyl group has inone embodiment from about 1 to about 100 carbon atoms, and in anotherembodiment from about 18 to about 33 carbon atoms, and in yet anotherembodiment about 30 carbon atoms, and in another embodiment about 50carbon atoms, wherein R if an aryl group has in one embodiment fromabout 5 to about 20 carbon atoms, and in another embodiment about 6carbon atoms, and in another embodiment about 10 carbon atoms, wherein Rif an alkylaryl group has in one embodiment about 7 carbon atoms, and inanother embodiment about 30 carbon atoms, and in yet another embodiment,about 50 carbon atoms, and in another embodiment about 100 carbon atoms,wherein R if an arylalkyl group has in one embodiment about 7 carbonatoms, and in another embodiment about 30 carbon atoms, and in anotherembodiment about 50 carbon atoms, and in another embodiment about 100carbon atoms, wherein in embodiments, R is a waxy chain, waxy as usedherein meaning containing at least about 10 carbon atoms, or at leastabout 18 carbon atoms, or from about 18 to about 100 carbon atoms, orfrom about 18 to about 33 carbon atoms, wherein in embodiments R is C₆H₅(phenyl), wherein in embodiments R is CH₂CH₂ (ethylene), wherein inembodiments R is OH, wherein in embodiments R is O—R (alkoxy), forexample, in embodiments, R is O—CH₃ (methoxy), wherein in embodiments Ris OAc, wherein OAc refers to any acetate moiety, and wherein inembodiments R is a co-polymer of maleic anhydride;

wherein n is an integer which is about 1 to about 1000, or about 1 toabout 20 or at least about 4, or at least about 12, or at least about50, and where m is an integer which is about 1 to about 1000, or about 1to about 20, or at least about 4, or at least about 12, or at leastabout 50;

wherein A is an anion, with examples of suitable anions including (butnot being limited to) Cl⁻, Br⁻, I⁻, HSO₄ ⁻, HSO₃ ⁻, SO₄2⁻, SO₃2⁻, CH₃SO₃⁻, CH₃C₆H₄SO₃ ⁻, NO₃ ⁻, HCOO⁻, CH₃COO⁻, H₂PO₄ ⁻, HPO₄2⁻, SCN⁻, BF₄ ⁻,ClO₄ ⁻, SSO₃ ⁻, PF₆ ⁻, SbCl₆ ⁻, or the like, as well as mixturesthereof, and

wherein CA is either a hydrogen atom or a cation with examples ofsuitable cations including (but not being limited to) alkali metalcations, such as Li+, Na+, K+, Rb+, and Cs+, nonpolymeric or monomericammonium and quaternary amine cations, including those of the generalformula

wherein each of R₂₁, R₂₂, R₂₃, and R₂₄, independently of the others, is(i) a hydrogen atom, (ii) an alkyl group (including linear, branched,saturated, unsaturated, cyclic, substituted, and unsubstituted alkylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe alkyl group), in one embodiment with at least 1 carbon atom, inanother embodiment with at least about 2 carbon atoms, in yet anotherembodiment with at least about 6 carbon atoms, in another embodimentwith at least about 8 carbon atoms, and in yet another embodiment withat least about 18 carbon atoms, and in one embodiment with no more thanabout 55 carbon atoms, in another embodiment with no more than about 30carbon atoms, and in yet another embodiment with no more than about 20carbon atoms, although the number of carbon atoms can be outside ofthese ranges, (iii) an aryl group (including unsubstituted andsubstituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur; silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about6 carbon atoms, in another embodiment with at least about 10 carbonatoms, and in yet another embodiment with at least about 14 carbonatoms, and in one embodiment with no more than about 26 carbon atoms, inanother embodiment with no more than about 22 carbon atoms, and in yetanother embodiment with no more than about 18 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iv) an arylalkylgroup (including unsubstituted and substituted arylalkyl groups, whereinthe alkyl portion of the arylalkyl group can be linear, branched,saturated, unsaturated, and/or cyclic, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the alkyl portion and thearyl portion of the arylalkyl group), in one embodiment with at leastabout 7 carbon atoms, in another embodiment with at least about 12carbon atoms, and in yet another embodiment with at least about 18carbon atoms, and in one embodiment with no more than about 55 carbonatoms, in another embodiment with no more than about 30 carbon atoms,and in yet another embodiment with no more than about 20 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas benzyl or the like, or (v) an alkylaryl group (includingunsubstituted and substituted alkylaryl groups, wherein the alkylportion of the alkylaryl group can be linear, branched, saturated,unsaturated, and/or cyclic, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in either or both of the alkyl portion and the arylportion of the alkylaryl group), in one embodiment with at least about 7carbon atoms, in another embodiment with at least about 12 carbon atoms,and in yet another embodiment with at least about 18 carbon atoms, andin one embodiment with no more than about 55 carbon atoms, in anotherembodiment with no more than about 30 carbon atoms, and in yet anotherembodiment with no more than about 20 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as tolyl or thelike, wherein one or more of R₂₁, R₂₂, R₂₃, and R₂₄ can be joinedtogether to form a ring, and wherein the substituents on the substitutedalkyl, aryl, arylalkyl, and alkylaryl groups can be (but are not limitedto) hydroxy groups, halogen atoms, amine groups, imine groups, ammoniumgroups, cyano groups, pyridine groups, pyridinium groups, ether groups,aldehyde groups, ketone groups, ester groups, amide groups, carbonylgroups, thiocarbonyl groups, sulfate groups, sulfonate groups, sulfonicacid groups, sulfide groups, sulfoxide groups, phosphine groups,phosphonium groups, phosphate groups, nitrile groups, mercapto groups,nitro groups, nitroso groups, sulfone groups, acyl groups, acidanhydride groups, azide groups, azo groups, cyanato groups, isocyanatogroups, thiocyanato groups, isothiocyanato groups, carboxylate groups,carboxylic acid groups, urethane groups, urea groups, mixtures thereof,and the like, wherein two or more substituents can be joined together toform a ring, oligomeric and polymeric cations, such as cationic polymersor oligomers, and the like, as well as mixtures thereof.

In one embodiment, the number of carbon atoms in R₁+R₂+R₃+R₄ is at leastabout 4, in another embodiment at least about 16, in another embodimentat least about 18, in yet another embodiment at least about 20, in stillanother embodiment at least about 22, in another embodiment at leastabout 24, in yet another embodiment at least about 26, in still anotherembodiment at least about 28, in another embodiment at least about 30,in yet another embodiment at least about 32, in still another embodimentat least about 34, in another embodiment at least about 36, in yetanother embodiment at least about 38, in still another embodiment atleast about 40, in another embodiment at least about 42, in yet anotherembodiment at least about 44, in still another embodiment at least about46, in another embodiment at least about 48, in yet another embodimentat least about 50, in still another embodiment at least about 52, inanother embodiment at least about 54, in yet another embodiment at leastabout 56, in still another embodiment at least about 58, in anotherembodiment at least about 60, in yet another embodiment at least about62, in still another embodiment at least about 64, in another embodimentat least about 66, in yet another embodiment at least about 68, in stillanother embodiment at least about 70, and in another embodiment at leastabout 72.

In some specific embodiments wherein

in one embodiment, the number of carbon atoms in R₁+R₂+R₃+R₄ is at leastabout 44, in still another embodiment at least about 46, in anotherembodiment at least about 48, in yet another embodiment at least about50, in still another embodiment at least about 52, in another embodimentat least about 54, in yet another embodiment at least about 56, in stillanother embodiment at least about 58, in another embodiment at leastabout 60, in yet another embodiment at least about 62, in still anotherembodiment at least about 64, in another embodiment at least about 66,in yet another embodiment at least about 68, in still another embodimentat least about 70, and in another embodiment at least about 72.

In some specific embodiments wherein

at least one of R₁, R₂, R₃, and R₄ is a group of the formula

wherein R₄₁ and R₄₂ each, independently of the other, is (i) an alkylgroup (including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkyl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the alkyl group), in one embodimentwith at least 1 carbon atom, and in another embodiment with at leastabout 2 carbon atoms, and in one embodiment with no more than about 55carbon atoms, in another embodiment with no more than about 30 carbonatoms, and in yet another embodiment with no more than about 20 carbonatoms, although the number of carbon atoms can be outside of theseranges, (ii) an aryl group (including unsubstituted and substituted arylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe aryl group), in one embodiment with at least about 6 carbon atoms,and in one embodiment with no more than about 26 carbon atoms, inanother embodiment with no more than about 22 carbon atoms, and in yetanother embodiment with no more than about 18 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iii) anarylalkyl group (including unsubstituted and substituted arylalkylgroups, wherein the alkyl portion of the arylalkyl group can be linear,branched, saturated, unsaturated, and/or cyclic, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in either or both of the alkylportion and the aryl portion of the arylalkyl group), in one embodimentwith at least about 7 carbon atoms, and in one embodiment with no morethan about 55 carbon atoms, in another embodiment with no more thanabout 30 carbon atoms, and in yet another embodiment with no more thanabout 20 carbon atoms, although the number of carbon atoms can beoutside of these ranges, such as benzyl or the like, or (iv) analkylaryl group (including unsubstituted and substituted alkylarylgroups, wherein the alkyl portion of the alkylaryl group can be linear,branched, saturated, unsaturated, and/or cyclic, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in either or both of the alkylportion and the aryl portion of the alkylaryl group), in one embodimentwith at least about 7 carbon atoms, and in one embodiment with no morethan about 55 carbon atoms, in another embodiment with no more thanabout 30 carbon atoms, and in yet another embodiment with no more thanabout 20 carbon atoms, although the number of carbon atoms can beoutside of these ranges, such as tolyl or the like, wherein one or moreof R₄₁ and R₄₂ can be joined together to form a ring, and wherein thesubstituents on the substituted alkyl, aryl, arylalkyl, and alkylarylgroups can be (but are not limited to) hydroxy groups, halogen atoms,amine groups, imine groups, ammonium groups, cyano groups, pyridinegroups, pyridinium groups, ether groups, aldehyde groups, ketone groups,ester groups, amide groups, carbonyl groups, thiocarbonyl groups,sulfate groups, sulfonate groups, sulfonic acid groups, sulfide groups,sulfoxide groups, phosphine groups, phosphonium groups, phosphategroups, nitrile groups, mercapto groups, nitro groups, nitroso groups,sulfone groups, acyl groups, acid anhydride groups, azide groups, azogroups, cyanato groups, isocyanato groups, thiocyanato groups,isothiocyanato groups, carboxylate groups, carboxylic acid groups,urethane groups, urea groups, mixtures thereof, and the like, whereintwo or more substituents can be joined together to form a ring,oligomeric and polymeric cations, such as cationic polymers oroligomers, and the like, as well as mixtures thereof.

In some specific embodiments wherein

at least one of R₁, R₂, R₃, and R₄ is a branched alkyl group having inone embodiment at least about 19 carbon atoms, and in another embodimentat least about 20 carbon atoms.

Since hetero atoms can be included in the alkyl, aryl, arylalkyl, andalkylaryl groups, and since the groups can be substituted, it is to beunderstood that R₁, R₂, R₃, R₄, R₅, R₆, R₈, R₉, and R₁₀ can also begroups such as alkoxy, polyalkyleneoxy, aryloxy, polyaryleneoxy,arylalkyloxy, polyarylalkyleneoxy, alkylaryloxy, or polyalkylaryleneoxygroups, provided that the oxygen atom in such a group is not directlybonded to a nitrogen, oxygen, or sulfur atom in the

central structure.

Examples of situations wherein one of the R1-4 groups is a cycloalkyl iswhen

Examples of situations wherein the R1-4 groups are joined together toform a ring are when

Examples of situations wherein one of the R1-4 groups is joined to aphenyl ring in the central structure is when

Compounds according to the present disclosure include rhodamines,wherein

of the general formula

acridines, wherein

of the general formula

sulforhodamines, wherein

of the general formula

anthracenes, wherein

of the general formula

and the like.

In a specific embodiment, the anion A can be an organic dianion of theformula A1-R11-A2 wherein A1 and A2 each, independently of the other,are anionic groups, such as carboxylate, sulfonate, or the like, andwherein R11 is (i) an alkylene group (including linear, branched,saturated, unsaturated, cyclic, substituted, and unsubstituted alkylenegroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe alkylene group), in one embodiment with at least 1 carbon atom, inanother embodiment with at least about 2 carbon atoms, in yet anotherembodiment with at least about 6 carbon atoms, in another embodimentwith at least about 8 carbon atoms, and in yet another embodiment withat least about 18 carbon atoms, and in one embodiment with no more thanabout 55 carbon atoms, in another embodiment with no more than about 30carbon atoms, and in yet another embodiment with no more than about 20carbon atoms, although the number of carbon atoms can be outside ofthese ranges, (ii) an arylene group (including unsubstituted andsubstituted arylene groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the arylene group), in one embodiment with at leastabout 6 carbon atoms, in another embodiment with at least about 10carbon atoms, and in yet another embodiment with at least about 14carbon atoms, and in one embodiment with no more than about 26 carbonatoms, in another embodiment with no more than about 22 carbon atoms,and in yet another embodiment with no more than about 18 carbon atoms,although the number of carbon atoms can be outside of these ranges,(iii) an arylalkylene group (including unsubstituted and substitutedarylalkylene groups, wherein the alkyl portion of the arylalkylene groupcan be linear, branched, saturated, unsaturated, and/or cyclic, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in either orboth of the alkyl portion and the aryl portion of the arylalkylenegroup), in one embodiment with at least about 7 carbon atoms, in anotherembodiment with at least about 12 carbon atoms, and in yet anotherembodiment with at least about 18 carbon atoms, and in one embodimentwith no more than about 55 carbon atoms, in another embodiment with nomore than about 30 carbon atoms, and in yet another embodiment with nomore than about 20 carbon atoms, although the number of carbon atoms canbe outside of these ranges, such as benzyl or the like, or (iv) analkylarylene group (including unsubstituted and substituted alkylarylenegroups, wherein the alkyl portion of the alkylarylene group can belinear, branched, saturated, unsaturated, and/or cyclic, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either or both of the alkylportion and the aryl portion of the alkylarylene group), in oneembodiment with at least about 7 carbon atoms, in another embodimentwith at least about 12 carbon atoms, and in yet another embodiment withat least about 18 carbon atoms, and in one embodiment with no more thanabout 55 carbon atoms, in another embodiment with no more than about 30carbon atoms, and in yet another embodiment with no more than about 20carbon atoms, although the number of carbon atoms can be outside ofthese ranges, such as tolyl or the like, and wherein the substituents onthe substituted alkylene, arylene, arylalkylene, and alkylarylene groupscan be (but are not limited to) hydroxy groups, halogen atoms, aminegroups, imine groups, ammonium groups, cyano groups, pyridine groups,pyridinium groups, ether groups, aldehyde groups, ketone groups, estergroups, amide groups, carbonyl groups, thiocarbonyl groups, sulfategroups, sulfonate groups, sulfonic acid groups, sulfide groups,sulfoxide groups, phosphine groups, phosphonium groups, phosphategroups, nitrile groups, mercapto groups, nitro groups, nitroso groups,sulfone groups, acyl groups, acid anhydride groups, azide groups, azogroups, cyanato groups, isocyanato groups, thiocyanato groups,isothiocyanato groups, carboxylate groups, carboxylic acid groups,urethane groups, urea groups, mixtures thereof, and the like, whereintwo or more substituents can be joined together to form a ring. Examplesof suitable organic dianions include unsubstituted and substitutednaphthalene disulfonates, unsubstituted and substituted benzenedisulfonates, and the like, as well as mixtures thereof.

In another specific embodiment, the anion A can be an organic trianion,tetraanion, and higher, an oligomeric and polymeric anion, such as apolysulfonate or polycarboxylate, or the like.

In one specific embodiment, the colorants according to the presentdisclosure are of the formula

In another specific embodiment, the colorants according to the presentdisclosure are of the formula

It is to be understood that in colorants of the formula

the positive charge is delocalized, and that other tautomeric structurescan be drawn, including (but not limited to)

and the like. It is to be understood that all possible tautomeric formsof these colorants are included within the above formulae.

Colorants of the present disclosure can be prepared by any desired oreffective procedure. For example, an α-olefin-maleic anhydride copolymer(for example, X5400, a 7000 MW copolymer available from the BakerPetrolite Corp.) having the desired R groups (which R groups will formthe polymer backbone of the present colorant and can be selected fromthe R groups of the of the present colorant as defined herein) can beadmixed with one or more aminophenols (for example,N,N-diethylaminophenol, MW=165, available from Aldrich Chemical Corp.)having the desired R₁, R₂, R₃, and R₄ groups, etc., thereon, with theR₁, R₂, R₃, and R₄ groups, etc., selected as defined for the colorantherein, heated, either neat or, optionally, in the presence of asolvent, after which an acid is added, for example conc. H₂SO₄ withadditional heating.

The α-olefin-maleic anhydride copolymer and the aminophenol are presentin any desired or effective relative amounts, in one embodiment at leastabout 0.5 mole of α-olefin-maleic anhydride copolymer per every 2 molesof aminophenol, in another embodiment at least about 0.8 mole ofα-olefin-maleic anhydride copolymer per every 2 moles of aminophenol,and in yet another embodiment at least about 1 mole of α-olefin-maleicanhydride copolymer per every 2 moles of aminophenol, and in oneembodiment no more than about 1.5 moles of α-olefin-maleic anhydridecopolymer per every 2 moles of aminophenol, in another embodiment nomore than about 2 moles of α-olefin-maleic anhydride copolymer per every2 moles of aminophenol, and in yet another embodiment no more than about6 moles of α-olefin-maleic anhydride copolymer per every 2 moles ofaminophenol, although the relative amounts can be outside of theseranges.

If desired, the reaction can be run neat, in the absence of a solvent.In addition, if desired, the reaction can be run in the presence of anoptional solvent. Examples of suitable solvents include tetramethylenesulfone (sulfolane), N-methyl pyrrolidone, dimethyl formamide, dimethylsulfoxide, octanol, or the like, as well as mixtures thereof. Whenpresent, the optional solvent is present in any desired or effectiveamount, in one embodiment at least about 1 liter per every 0.1 mole ofα-olefin-maleic anhydride copolymer, in another embodiment at leastabout 1 liter per every 0.3 mole of α-olefin-maleic anhydride copolymer,and in yet another embodiment at least about 1 liter per every 0.35 moleof α-olefin-maleic anhydride copolymer, and in one embodiment no morethan about 1 liter per every 2 moles of α-olefin-maleic anhydridecopolymer, in another embodiment no more than about 1 liter per every1.5 moles of α-olefin-maleic anhydride copolymer, and in yet anotherembodiment no more than about 1 liter per every 1 mole ofα-olefin-maleic anhydride copolymer, although the relative amounts canbe outside of these ranges.

The mixture of α-olefin-maleic anhydride copolymer, aminophenol, andoptional solvent is then heated to any effective temperature, in oneembodiment at least about 62° C., in another embodiment at least about150° C., and in yet another embodiment at least about 190° C., and inone embodiment no more than about 280° C., in another embodiment no morethan about 220° C., and in yet another embodiment no more than about200° C., although the temperature can be outside of these ranges.

The mixture of α-olefin-maleic anhydride copolymer, aminophenol, andoptional solvent is heated for any effective period of time, in oneembodiment at least about 5 minutes, in another embodiment at leastabout 2 hours, and in yet another embodiment at least about 3 hours, andin one embodiment no more than about 4 days, in another embodiment nomore than about 60 hours, and in yet another embodiment no more thanabout 40 hours, although the time can be outside of these ranges.

In embodiments, acid can be added for example in an amount of about 1mole of acid for each 2 moles of aminophenol. The acid is then added andthe mixture heated for any to any effective temperature, in oneembodiment at least about 62° C., in another embodiment at least about150° C., and in yet another embodiment at least about 190° C., and inone embodiment no more than about 280° C., in another embodiment no morethan about 220° C., and in yet another embodiment no more than about200° C., although the temperature can be outside of these ranges.

The mixture of α-olefin-maleic anhydride copolymer, aminophenol,optional solvent, and acid is heated for any effective period of time,in one embodiment at least about 5 minutes, in another embodiment atleast about 1 hour, in another embodiment at least about 2 hours, and inyet another embodiment at least about 3 hours, and in another embodimentabout 14 hours, although the time can be outside of these ranges.

If desired, the resulting product can be purified by pouring thereaction mixture into an organic non-water-soluble andnon-water-miscible solvent in which the product is soluble or miscibleand in which undesirable salt byproducts are not soluble, such as methylisobutyl ketone, toluene, hexane, heptane, or the like, followed byadmixing the solvent containing the product with water in a separatoryfunnel and separating the aqueous and organic phases.

The crude product can then, if desired, be further purified by washingit with aqueous EDTA to remove metal salts, followed by washing withwater. If desired, a titration or other instrumental technique, such asAA (atomic absorption) or ICP (inductively coupled plasma) can beperformed to determine if the metal salts have been completely removed.The purified product can be isolated by distilling off any solvents.

Various substituents can be placed on the rings of the colorants of thepresent disclosure by any desired or effective method, such as, forexample, the methods disclosed in U.S. Pat. No. 5,847,162 and U.S. Pat.No. 1,991,482, the disclosures of each of which are totally incorporatedherein by reference. See for example, U.S. patent application Ser. No.10/607,382, published Jan. 20, 2005, and U.S. Pat. No. 6,860,931, thedisclosures of each of which are hereby incorporated by reference hereinin their entireties.

In embodiments, transformations can be effected to produce alternateproducts. For example, in embodiments, the following reaction

wherein in embodiments R₃₀ and R₃₁ each, independently of the other, isan alkyl group, an aryl group, an alkylaryl group, or an arylalkylgroup, wherein in embodiments R₃₀ and R₃₁ are each, independently of theother, selected from an alkyl group having from about 1 to about 100carbon atoms, or about 18 to about 33 carbon atoms, or about 30 carbonatoms, or about 50 carbon atoms, an aryl group having from about 5 toabout 20 carbon atoms, or about 6 carbon atoms, or about 10 carbonatoms, an alkylaryl group having about 7 carbon atoms or about 30 carbonatoms, or about 50 carbon atoms, or about 100 carbon atoms, or anarylalkyl group having from about 7 carbon atoms, or about 30 carbonatoms, or about 50 carbon atoms, or about 100 carbon atoms, wherein inembodiments R is a waxy chain, waxy as used herein meaning containing atleast about 10 carbon atoms, or at least about 18 carbon atoms, or fromabout 18 to about 100 carbon atoms, or from about 18 to about 33 carbonatoms, wherein in embodiments R Is CH, (phenyl), wherein n is an integerwhich is about 1 to about 1000, or about 1 to about 20 or at least about4, or at least about 12, or at least about 50, and where m is an integerwhich is about 1 to about 1000, or about 1 to about 20, or at leastabout 4, or at least about 12, or at least about 50; p is an integerwhich is about 1 to about 1000, or about 1 to about 20, or at leastabout 4, or at least about 12, or at least about 50, and s is an integerwhich is about 1 to about 1000, or about 1 to about 20 or at least about4, or at least about 12, or at least about 50.

In another embodiment,

wherein in embodiments R₃₀ and R₃₁ each, independently of the other, isan alkyl group, an aryl group, an alkylaryl group, or an arylalkylgroup, wherein in embodiments R₃₀ and R₃₁ are each, independently of theother, selected from an alkyl group having from about 1 to about 100carbon atoms, or about 18 to about 33 carbon atoms, or about 30 carbonatoms, or about 50 carbon atoms, an aryl group having from about 5 toabout 20 carbon atoms, or about 6 carbon atoms, or about 10 carbonatoms, an alkylaryl group having about 7 carbon atoms or about 30 carbonatoms, or about 50 carbon atoms, or about 100 carbon atoms, or anarylalkyl group having from about 7 carbon atoms, or about 30 carbonatoms, or about 50 carbon atoms, or about 100 carbon atoms, wherein inembodiments R is a waxy chain, waxy as used herein meaning containing atleast about 10 carbon atoms, or at least about 18 carbon atoms, or fromabout 18 to about 100 carbon atoms, or from about 18 to about 33 carbonatoms, wherein in embodiments R Is C₆H₅ (phenyl), wherein n is aninteger which is about 1 to about 1000, or about 1 to about 20 or atleast about 4, or at least about 12, or at least about 50, and where mis an integer which is about 1 to about 1000, or about 1 to about 20, orat least about 4, or at least about 12, or at least about 50; p is aninteger which is about 1 to about 1000, or about 1 to about 20, or atleast about 4, or at least about 12, or at least about 50, and s is aninteger which is about 1 to about 1000, or about 1 to about 20 or atleast about 4, or at least about 12, or at least about 50.

In yet another embodiment,

wherein in embodiments R₃₀ and R₃₁ each, independently of the other, isan alkyl group, an aryl group, an alkylaryl group, or an arylalkylgroup, wherein in embodiments R₃₀ and R₃₁ are each, independently of theother, selected from an alkyl group having from about 1 to about 100carbon atoms, or about 18 to about 33 carbon atoms, or about 30 carbonatoms, or about 50 carbon atoms, an aryl group having from about 5 toabout 20 carbon atoms, or about 6 carbon atoms, or about 10 carbonatoms, an alkylaryl group having about 7 carbon atoms or about 30 carbonatoms, or about 50 carbon atoms, or about 100 carbon atoms, or anarylalkyl group having from about 7 carbon atoms, or about 30 carbonatoms, or about 50 carbon atoms, or about 100 carbon atoms, wherein inembodiments R is a waxy chain, waxy as used herein meaning containing atleast about 10 carbon atoms, or at least about 18 carbon atoms, or fromabout 18 to about 100 carbon atoms, or from about 18 to about 33 carbonatoms, wherein in embodiments R Is C₆H₅ (phenyl), wherein n is aninteger which is about 1 to about 1000, or about 1 to about 20 or atleast about 4, or at least about 12, or at least about 50, and where mis an integer which is about 1 to about 1000, or about 1 to about 20, orat least 4, or at least 12, or at least 50; p is an integer which isabout 1 to about 1000, or about 1 to about 20, or at least about 4, orat least about 12, or at least about 50, and s is an integer which isabout 1 to about 1000, or about 1 to about 20 or at least about 4, or atleast about 12, or at least about 50.

EXAMPLES

The following Examples are being submitted to further define variousspecies of the present disclosure. These Examples are intended to beillustrative only and are not intended to limit the scope of the presentdisclosure. Also, parts and percentages are by weight unless otherwiseindicated.

Example 1

An α-olefin-maleic anhydride copolymer (50 grams, X5400®, a 7000 MWcopolymer obtained from Baker Petrolite Corporation) of the formula

was placed in a 350 milliliter beaker with magnet and the beaker wasplaced in a 150° C. oil bath and allowed to melt at which time stirringwas initiated. About 28.3 grams N,N-diethylaminophenol (a 75 MWaminophenol obtained from Aldrich Chemical Co.) of the formula

was then added and a watch glass placed over the beaker and the contentsallowed to stir at 150° C. for 3 hours. About 2.5 grams of concentratedH₂SO₄ was then added and allowed to stir an additional 1 hour. Themolten contents were then poured into a 1 liter beaker containing 500milliliters of methanol. The solids were then transferred to a mortarand pestle and ground into a fine magenta powder. The powder was placedin a 500 milliliter beaker with 300 milliliters of methanol and heatedand stirred to a boil. The beaker was removed from the heat and filteredthrough a Buchner funnel and the solid magenta polymer was collected.The Zwitterionic form of this colorant is believed to be of the formula

Other synthetic processes can also be used.

Example 2

Synthesis of Octadecenyl Succinic Anhydride Based Rhodamine

An α-olefin-maleic anhydride copolymer (50 grams, X5400®, a 7000 MWcopolymer obtained from Baker Petromte Corporation) of the formula

was placed in a 350 milliliter beaker with magnet and the beaker wasplaced in a 150° C. oil bath and allowed to melt at which time stirringwas initiated. About 25.4 grams N,N-diethylphenol (a 221 MW aminophenolobtained from TCI America) of the formula

was then added and a watch glass placed over the beaker and the contentsallowed to stir at 150° C. for 3 hours. About 5.6 grams of concentratedH₂SO₄ was then added and allowed to stir an additional 1 hour. Themolten contents were then poured into a 1 liter beaker containing 500milliliters of methanol. The solids were then transferred to a mortarand pestle and ground into a fine magenta powder. The powder was placedin a 500 milliliter beaker with 300 milliliters of methanol and heatedand stirred to a boil. The beaker was removed from the heat and filteredthrough a Buchner funnel and the solid magenta polymer was collected.The Zwitterionic form of this colorant is believed to be of the formula

Example 3

Preparation of an Ink Base

An ink base was prepared by melting, admixing, and filtering thefollowing ingredients:

43.59 parts by weight polyethylene wax (PE 655®, obtained from BakerPetrolite) of the formula CH₃(CH₂)₅₀CH₃);

19.08 parts by weight stearyl stearamide wax (KEMAMIDE® S-180, obtainedfrom Crompton Corporation);

18.94 parts by weight tetra-amide resin obtained from the reaction ofone equivalent of a C-36 dimer acid (obtained from Uniqema, New Castle,Del.) with two equivalents of ethylene diamine and UNICID® 700 (obtainedfrom Baker Petrolite), a long chain hydrocarbon having a terminalcarboxylic acid group, prepared as described in Example 1 of U.S. Pat.No. 6,174,937, which is hereby incorporated by reference herein in itsentirety;

11.71 parts by weight urethane resin obtained from the reaction of twoequivalents of ABITOL® E hydroabietyl alcohol (obtained from HerculesInc.) and one equivalent of isophorone diisocyanate, prepared asdescribed in Example 1 of U.S. Pat. No. 5,782,966, which is herebyincorporated by reference herein;

6.48 parts by weight urethane resin that is the adduct of threeequivalents of stearyl isocyanate and a glycerol-based alcohol, preparedas described in Example 4 of U.S. Pat. No. 6,309,453, which is herebyincorporated by reference herein in its entirety;

0.20 parts by weight NAUGUARD® 445 antioxidant (obtained from UniroyalChemical Co.).

Thereafter, 600 grams of the ink carrier components as listed above inthe percentages as listed above were added to a 1 liter beaker andheated in an oven at 135° C. until molten. Subsequently, the beaker wasinserted into a heating mantle set to 135° C. and the contents of thebeaker were stirred for 45 minutes. The resulting ink was then filteredthrough a combination of Whatman #3 and 0.2 micron NAE filters andplaced in a Mott filter assembly. Filtration was supported by theaddition of 1 percent by weight FILTER-AID obtained from Fluka Chemika,and proceeded at a temperature of 135 C until complete after 6 hours.The ink base was poured into molds containing about 31 grams of thecolorless ink base and allowed to cool.

Example 4 Preparation of Ink Containing Colorant

About 30.0 grams of ink base from Example 3 was placed in a 100milliliter beaker with a magnetic stir bar and subsequently placed in a135 C oil bath until molten. About 2.0 grams of the product of Example 1was then added and stirred for about 3 hours. The magenta colorant wasthen poured into an aluminum mold.

Example 5 Preparation of Ink Containing Colorant

About 30.0 grams of ink base from Example 3 was placed in a 100milliliter beaker with a magnetic stir bar and subsequently placed in a135 C oil bath until molten. About 2.0 grams of the product of Example 2was then added and stirred for about 3 hours. The magenta colorant wasthen poured into an aluminum mold.

Example 6 Printing of Ink Samples Containing Colorant

Printed samples of the inks prepared in Examples 4 and 5 were generatedon HAMMERMILL LASERPRINT® paper using a K Printing Proofer (manufacturedby RK Print Coat Instrument Ltd., Litlington, Royston, Heris, SG8 0OZ,U.K.). In this method, the tested inks were melted onto a printing plateset at 150° C. temperature. A roller bar fitted with the paper was thenrolled over the plate containing the melted ink on its surface. The inkon the paper was cooled, resulting in three separated images ofrectangular blocks. The most intensely colored block contained the mostink deposited on the paper, and was therefore used to obtain the colorvalue measurements. The printed samples were evaluated visually.

It will be appreciated that various of the above-disclosed and otherfeatures and functions, or alternatives thereof, may be desirablycombined into many other different systems or applications. Also thatvarious presently unforeseen or unanticipated alternatives,modifications, variations or improvements therein may be subsequentlymade by those skilled in the art which are also intended to beencompassed by the following claims. Unless specifically recited in aclaim, steps or components of claims should not be implied or importedfrom the specification or any other claims as to any particular order,number, position, size, shape, angle, color, or material.

1. A compound of the formula

wherein R₁, R₂, R₃, and R₄ each, independently of the others, is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group, wherein R₁ and R₂ can bejoined together to form a ring, wherein R₃ and R₄ can be joined togetherto form a ring, and wherein R₁, R₂, R₃, and R₄ can each be joined to aphenyl ring in the central structure; wherein a and b each,independently of the others, is an integer which is 0, 1, 2, or 3,wherein each R₅, and R₆ independently of the other, is (i) an alkylgroup, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylarylgroup, (v) a halogen atom, (vi) an ester group, (vii) an amide group,(viii) a sulfone group, (ix) an amine group or ammonium group, (x) anitrile group, (xi) a nitro group, (xii) a hydroxy group, (xiii) a cyanogroup, (xiv) a pyridine or pyridinium group, (xv) an ether group, (xvi)an aldehyde group, (xvii) a ketone group, (xviii) a carbonyl group,(xix) a thiocarbonyl group, (xx) a sulfate group, (xxi) a sulfide group,(xxii) a sulfoxide group, (xxiii) a phosphine or phosphonium group,(xxiv) a phosphate group, (xxv) a mercapto group, (xxvi) a nitrosogroup, (xxvii) an acyl group, (xxviii) an acid anhydride group, (xxix)an azide group, (xxx) an azo group, (xxxi) a cyanato group, (xxxii) anisocyanato group, (xxxiii) a thiocyanato group, (xxxiv) anisothiocyanato group, (xxxv) a urethane group, (xxxvi) a urea group, or(xxxvii) hydrogen, wherein R₅ and R₆ can each be joined to a phenyl ringin the central structure,

wherein R₈, R₉, and R₁₀ each, independently of the other, is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group; wherein A is an anion;wherein CA is either a hydrogen atom or a cation; wherein R is (i) analkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) analkylaryl group, (v) an alkoxy group, (vi) an acetate group, or (vii) aco-polymer of maleic anhydride; wherein n is an integer which is about 1to about 1,000; and wherein m is an integer which is about 1 to about1,000.
 2. A compound according to claim 1, wherein a and b are eachzero.
 3. A compound according to claim 1, wherein


4. A compound according to claim 1, wherein


5. A compound according to claim 1, wherein


6. A compound according to claim 1, wherein


7. A compound according to claim 1, wherein A- is an organic dianion ofthe formula A1-R11-A2 wherein A1 and A2 each, independently of theother, are anions and wherein R11 is (i) an alkylene group, (ii) anarylene group, (iii) an arylalkylene group, or (iv) an alkylarylenegroup.
 8. A compound according to claim 1, wherein at least one of R₁,R₂, R₃, and R₄ is an alkyl group.
 9. A compound according to claim 8,wherein the alkyl group is a linear alkyl group.
 10. A compoundaccording to claim 8, wherein the alkyl group is a branched alkyl group.11. A compound according to claim 8, wherein the alkyl group is asaturated alkyl group.
 12. A compound according to claim 8, wherein thealkyl group is an unsaturated alkyl group.
 13. A compound according toclaim 8, wherein the alkyl group is a cyclic alkyl group.
 14. A compoundaccording to claim 8, wherein the alkyl group is a substituted alkylgroup.
 15. A compound according to claim 8, wherein the alkyl group isan unsubstituted alkyl group.
 16. A compound according to claim 1,wherein at least one of R₁, R₂, R₃, and R₄ is an aryl group.
 17. Acompound according to claim 16, wherein the aryl group is a substitutedaryl group.
 18. A compound according to claim 16, wherein the aryl groupis an unsubstituted aryl group.
 19. A compound according to claim 1,wherein R₁ and R₂ are joined together to form a ring.
 20. A compoundaccording to claim 1, wherein R₁ and R₂ are joined together to form aring and wherein R₃ and R₄ are joined together to form a ring.
 21. Acompound according to claim 1, wherein at least one of R₁, R₂, R₃, andR₄ is joined to a phenyl ring in the central structure.
 22. A compoundaccording to claim 1, wherein R is an alkyl group.
 23. A compoundaccording to claim 1, wherein R is an aryl group.
 24. A compoundaccording to claim 1, wherein R is an alkylaryl group.
 25. A compoundaccording to claim 1, wherein R is an arylalkyl group.
 26. A compoundaccording to claim 1, wherein R has from about 1 to about 100 carbonatoms.
 27. A compound according to claim 1, wherein R has from about 18to about 33 carbon atoms.
 28. A compound according to claim 1, wherein Ris C₆H₅.
 29. A compound according to claim 1, wherein R is CH₂CH₂.
 30. Acompound of the formula

wherein n is about 1 to about 1,000 and wherein m is about 1 to about1,000.
 31. A compound of the formula

wherein n is about 1 to about 1,000 and wherein m is about 1 to about1,000.
 32. A compound according to claim 1, of the formula

wherein R₃₀ and R₃₁ each, independently of the other, is an alkyl group,an aryl group, an alkylaryl group, or an arylalkyl group; and wherein nis about 1 to about 1,000, m is about 1 to about 1,000, p is about 1 toabout 1,000, and s is about 1 to about 1,000.
 33. A compound accordingto claim 1, of the formula

wherein R₃₀ and R₃₁ each, independently of the other, is an alkyl group,an aryl group, an alkylaryl group, or an arylalkyl group; and wherein nis about 1 to about 1,000, m is about 1 to about 1,000, p is about 1 toabout 1,000, and s is about 1 to about 1,000.
 34. A compound accordingto claim 1, of the formula

wherein R₃₀ and R₃₁ each, independently of the other, is an alkyl group,an aryl group, an alkylaryl group, or an arylalkyl group; and wherein nis about 1 to about 1,000, m is about 1 to about 1,000, p is about 1 toabout 1,000, and s is about 1 to about 1,000.